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Issue 2, 2015
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Suzuki–Miyaura coupling of arylboronic acids to gold(III)

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Abstract

Gold(III) is prominent in catalysis, but its organometallic chemistry continues to be restricted by synthesis. Metal–carbon bond formation often relies on organometallic complexes of electropositive elements, including lithium and magnesium. The redox potential of gold(III) interferes with reactions of these classic reagents. Resort to toxic metals is common, including reagents based on mercury and thallium. We report that the palladium-catalyzed Suzuki–Miyaura coupling of arylboronic acids extends to cyclometalated gold(III) chlorides. Both monoarylation and diarylation are achieved. We propose a mechanism where oxidative addition to palladium with rearrangement at gold(III) fixes the stereochemistry of monoarylated intermediates. Singly arylated species form as thermodynamic isomers. These entities then go on to form diarylated complexes. Reactions proceed at room temperature, and the products are stable to air, moisture, and chromatography.

Graphical abstract: Suzuki–Miyaura coupling of arylboronic acids to gold(iii)

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Publication details

The article was received on 18 Jul 2014, accepted on 27 Oct 2014 and first published on 06 Nov 2014


Article type: Edge Article
DOI: 10.1039/C4SC02148G
Citation: Chem. Sci., 2015,6, 981-986
  • Open access: Creative Commons BY-NC license
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    Suzuki–Miyaura coupling of arylboronic acids to gold(III)

    A. Maity, A. N. Sulicz, N. Deligonul, M. Zeller, A. D. Hunter and T. G. Gray, Chem. Sci., 2015, 6, 981
    DOI: 10.1039/C4SC02148G

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